Is there anything I need to know, is this even possible, more importantly would it even be worth it??

When I say good I guess my parameters would be the usual items like protection, anonymity (if that's even a thing) etc...Thank you in advance!

Looking back, I regret not buying another flip, or even a smaller house as a future rental. 

Creating a holding company, LLC, business cards, websites, and all this other nonsense is like buying an indoor basketball court so you can pursue your dream of playing in the NBA . . . before you even try a pickup game to see if you are any good or like the sport.Buy an investment property and learn how to manage it.

And the neighborhood is even more critical as he said.I'd bet even a veteran Contr like Mr Paul would hesitate before giving a rehab $$ number based on a video alone.It will take you years of actual doing before you could even get a number from a walk-through.

I have religiously listened to the BiggerPockets Pod cast for a long time and even read some of the books.

Don't even get me started on passive investor door counts.

The mortgage payment on this house was roughly $1800/month so when we get tenants (or technically roommates while we're still living in the house) we figure we would have them split the rent evenly, or as a percentage of the house since someone could have the entire basement to themselves.

Also your lender should make you aware of the fact that you can even get an income credit for the departing residence to help you qualify for the new place.  

Even a 30 year note usually pays off in an average of 7-10 years.